Methylparaben

Last updated
Methylparaben
Methylparaben.svg
Methylparaben.png
Names
Preferred IUPAC name
Methyl 4-hydroxybenzoate
Other names
  • Methyl paraben
  • Methyl p-hydroxybenzoate
  • Methyl parahydroxybenzoate
  • Nipagin M
  • E number E218
  • Tegosept
  • Mycocten
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.532 OOjs UI icon edit-ltr-progressive.svg
E number E218 (preservatives)
KEGG
PubChem CID
UNII
  • InChI=1S/C8H8O3/c1-11-8(10)6-2-4-7(9)5-3-6/h2-5,9H,1H3 Yes check.svgY
    Key: LXCFILQKKLGQFO-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C8H8O3/c1-11-8(10)6-2-4-7(9)5-3-6/h2-5,9H,1H3
    Key: LXCFILQKKLGQFO-UHFFFAOYAH
  • COC(=O)c1ccc(O)cc1
Properties
C8H8O3
Molar mass 152.149 g·mol−1
AppearanceColorless crystals or white crystalline powder [1]
Density 1.383 g/cm3
Melting point 131 °C (268 °F; 404 K)
Boiling point 265 °C (509 °F; 538 K)
UV-vis (λmax)255 nm (methanol)
−88.7·10−6 cm3/mol
Hazards
NFPA 704 (fire diamond)
NFPA 704.svgHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
1
0
Related compounds
Related Parabens
Ethylparaben
Propylparaben
Butylparaben
Related compounds
 Methyl salicylate (ortho isomer)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)
UV-visible spectrum of methylparaben Methylparaben UV-vis spectrum.png
UV-visible spectrum of methylparaben

Methylparaben (methyl paraben) one of the parabens, is a preservative with the chemical formula CH3O2CC6H4OH. It is the methyl ester of p-hydroxybenzoic acid. Several related esters are known (ethyl-, propyl-, butylparaben). Together they are the most common preservatives in cosmetics and foods. Among their advantages, parabens are inexpensive, colorless, stable, odorless, and readily biodegraded. [2]

Contents

Natural occurrences

Methylparaben serves as a pheromone for a variety of insects [3] and is a component of queen mandibular pheromone.

It is a pheromone in wolves produced[ clarification needed ] during estrus associated with the behavior of alpha male wolves preventing other males from mounting females in heat. [4] [5]

Uses

Methylparaben is an anti-fungal agent often used in a variety of cosmetics and personal-care products. It is also used as a food preservative and has the E number E218.

Methylparaben is commonly used as a fungicide in Drosophila food media at 0.1%. [6] To Drosophila, methylparaben is toxic at higher concentrations, has an estrogenic effect (mimicking estrogen in rats and having anti-androgenic activity), and slows the growth rate in the larval and pupal stages at 0.2%. [7]

Safety

Methylparaben is practically non-toxic by both oral and parenteral administration in animals. [8] In a population with normal skin, methylparaben is practically non-irritating and non-sensitizing; however, allergic reactions to ingested parabens have been reported. [8] A 2008 study found no competitive binding for human estrogen and androgen receptors for methylparaben, but varying levels of competitive binding were seen with butyl- and isobutyl-paraben. [9]

Some controversy exists about whether methylparaben or propylparabens are harmful at concentrations typically used in body care or cosmetics. [10] Methylparaben and propylparaben are considered generally recognized as safe (GRAS) by the USFDA for food and cosmetic antibacterial preservation. [11] Methylparaben is readily metabolized by common soil bacteria, making it completely biodegradable.

Methylparaben is readily absorbed from the gastrointestinal tract or through the skin. [8] It is hydrolyzed to p-hydroxybenzoic acid and rapidly excreted in urine without accumulating in the body. [8]

Methylparaben applied on the skin may react with UVB, leading to increased skin aging and DNA damage. [12] [13]

References

  1. ↑ "Methylparaben Experimental Properties". PubChem.
  2. ↑ Matwiejczuk, Natalia; Galicka, Anna; Brzóska, Małgorzata M. (2020). "Review of the safety of application of cosmetic products containing parabens". Journal of Applied Toxicology. 40 (1): 176–210. doi:10.1002/jat.3917. PMID   31903662.
  3. ↑ "Semiochemical - me-4-hydroxybenzoate". pherobase.com.
  4. ↑ Mertl-Millhollen, Anne S.; Goodmann, Patricia A.; Klinghammer, Erich (1986). "Wolf scent marking with raised-leg urination". Zoo Biology. 5: 7–20. doi:10.1002/zoo.1430050103.
  5. ↑ Steven R. Lindsay (2013). Handbook of Applied Dog Behavior and Training, Adaptation and Learning. John Wiley and Sons.
  6. ↑ "Bloomington Drosophila Stock Center".
  7. ↑ Gu W, Xie DJ, Hour XW (2009). "Toxicity and Estrogen Effects of Methyl Paraben on Drosophila melanogaster". Food Science. 30 (1): 252–254.
  8. 1 2 3 4 Soni MG, Taylor SL, Greenberg NA, Burdock GA (October 2002). "Evaluation of the health aspects of methyl paraben: a review of the published literature". Food and Chemical Toxicology. 40 (10): 1335–73. doi:10.1016/S0278-6915(02)00107-2. PMID   12387298.
  9. ↑ Alan AF (2008). "Final amended report on the safety assessment of Methylparaben, Ethylparaben, Propylparaben, Isopropylparaben, Butylparaben, Isobutylparaben, and Benzylparaben as used in cosmetic products". International Journal of Toxicology. 27 Suppl 4 (Suppl 4): 1–82. doi:10.1080/10915810802548359. PMID   19101832.
  10. ↑ Haman, Camille; Dauchy, Xavier; Rosin, Christophe; Munoz, Jean-François (2015). "Occurrence, fate and behavior of parabens in aquatic environments: A review". Water Research. 68: 1–11. Bibcode:2015WatRe..68....1H. doi:10.1016/j.watres.2014.09.030. PMID   25462712.
  11. ↑ "Parabens". Food and Drug Administration. 9 September 2020. Archived from the original on March 30, 2014.
  12. ↑ Handa O, Kokura S, Adachi S, Takagi T, Naito Y, Tanigawa T, et al. (October 2006). "Methylparaben potentiates UV-induced damage of skin keratinocytes". Toxicology. 227 (1–2): 62–72. Bibcode:2006Toxgy.227...62H. doi:10.1016/j.tox.2006.07.018. PMID   16938376.
  13. ↑ Okamoto Y, Hayashi T, Matsunami S, Ueda K, Kojima N (August 2008). "Combined activation of methyl paraben by light irradiation and esterase metabolism toward oxidative DNA damage". Chemical Research in Toxicology. 21 (8): 1594–9. doi:10.1021/tx800066u. PMID   18656963.
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